Although much better known for his opinions regarding constitutional law and individual rights, Justice William O. Douglas also left an indelible mark in tax law. Throughout his thirty-six year tenure on the Supreme Court, Douglas wrote a significant number of majority and dissenting opinions in some of the most famous tax law cases of his day. As the title of the article suggests, most of Douglas's opinions were full of spin from the bias of the party he favored and read more like a brief than an objective Court opinion. In additionto their obvious spin, Douglas's opinions often lacked well-reasoned analysis, ignored compelling counter-arguments made by his brethren in dissenting and majority opinions, misconstrued, minimalized, or completely ignored contrary judicial and legislative authority. In many instances, Douglas's majority opinions frequently crossed the line of judicial interpretation into judicial legislation with absurd outcomes and punitive consequences to the taxpayer or the government. In addition to Douglas's dubious legacy as a “spin” Justice in tax controversies, Douglas also wrote poorly reasoned majority opinions that were difficult to comprehend and provided little guidance to the taxpayer and the government.

The purpose of this Article is to critique the judicial evolution of Douglas as a “rogue” Justice in tax controversies through a comprehensive analysis of a cross section of Douglas's prominent majority and dissenting opinions in the three distinct periods of his judicial tenure. Those periods were (1) the Pro-Commissioner Period (1939-1944) in which Douglas's opinions were decidedly spun for the Commissioner regardless of the inequitable consequences to the taxpayer; (2) the Pro-Taxpayer Period (1944-1958) in which Douglas's allegiance shifted from the Commissioner to the taxpayer as reflected in his opinions delivered throughout that period; and (3) the Taxpayer Advocate Period (1958-1975) in which Douglas's Pro-Taxpayer opinions were as extremely slanted in favor of the taxpayer as they were in favor of the Commissioner during the Pro-Commissioner Period.